US20050048191A1 - Dextrinized, saccharide-derivatized oligosaccharides - Google Patents

Dextrinized, saccharide-derivatized oligosaccharides Download PDF

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Publication number
US20050048191A1
US20050048191A1 US10/874,686 US87468604A US2005048191A1 US 20050048191 A1 US20050048191 A1 US 20050048191A1 US 87468604 A US87468604 A US 87468604A US 2005048191 A1 US2005048191 A1 US 2005048191A1
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US
United States
Prior art keywords
saccharide
mixture
oligosaccharide
oligosaccharides
polymerization
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/874,686
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English (en)
Inventor
Richard Antrim
Frank Barresi
Roger McPherson
Jiao Wang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Grain Processing Corp
Original Assignee
Grain Processing Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Grain Processing Corp filed Critical Grain Processing Corp
Priority to US10/874,686 priority Critical patent/US20050048191A1/en
Assigned to GRAIN PROCESSING CORPORATION reassignment GRAIN PROCESSING CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BARRESI, FRANK W., MCPHERSON, ROGER E., WANG, JIAO, ANTRIM, RICHARD L.
Publication of US20050048191A1 publication Critical patent/US20050048191A1/en
Priority to US11/292,246 priority patent/US20060149053A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/37—Sugar alcohols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
    • A23L33/25—Synthetic polymers, e.g. vinylic or acrylic polymers
    • A23L33/26—Polyol polyesters, e.g. sucrose polyesters; Synthetic sugar polymers, e.g. polydextrose
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
    • C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
    • C08B30/18—Dextrin, e.g. yellow canari, white dextrin, amylodextrin or maltodextrin; Methods of depolymerisation, e.g. by irradiation or mechanically
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L9/00—Puddings; Cream substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • dextrinized saccharide-derivatized oligosaccharides may be prepared, and that such products can function as bulking agents or as slow energy release compounds.
  • an oligosaccharide which most preferably is a malto-oligosaccharide, is dextrinized by extrusion in the presence of a saccharide.
  • the dextrinized oligosaccharide product and the process for its preparation offer a number of completely unexpected properties and advantages not heretofore realized.
  • the product has low digestibility, and thus is suitable in a number of applications as a bulking agent, a product carrier, or the like.
  • the present invention provides a mixture of saccharide-derivatized oligosaccharides prepared by extruding a reaction mixture that includes a saccharide having a degree of polymerization ranging from 1 to 4, a first oligosaccharide having a degree of polymerization of at least 5, and a second oligosaccharide having a degree of polymerization of at least 20, wherein the extruding imparts sufficient energy and force to derivatize the first oligosaccharide with the saccharide.
  • the resistance to color formation of the reduced malto-oligosaccharide is improved relative to the starting mixture of unreduced malto-oligosaccharides.
  • a liquid mixture of the reduced malto-oligosaccharides will be stable, and, it is believed, relatively more stable than a liquid mixture of unreduced malto-oligosaccharides.
  • Vacuum optionally can be applied to the system; if applied, up to 18 inches of mercury (0.4 atm) can be used.
  • the foregoing set of conditions is by no means meant to be exhaustive or limiting, but to the contrary these conditions are provided for general guidance.
  • the actual extruder conditions can vary widely depending on the starting materials and the type of extruder being used.
  • Percentage maltodextrin and dextrose were expressed on a dry solids basis per total weight (maltodextrin and dextrose).
  • the dextrose value represents dextrose added to the malto-oligosaccharide.
  • the extruded product was a puffy, golden yellow solid material.
  • the material was allowed to cool and ground to a golden yellow powder.
  • the samples were analyzed yielding the following results. Color measurements are dyed on the international standard promulgated by the Commission Internationale d'Eclairage (CIE) Max Shaft MD Citric Temp. Speed % Motor Example type MD % Dextrose Acid ° C.
  • CIE Commission Internationale d'Eclairage
  • a sweetener is prepared by blending 700 g of the spray-dried product of Example 25 with 300 g of sucralose.
  • a 70/30/1 Limit Dextrin/Dextrose (anhydrous)/citric acid blend was made by mixing 700 g of limit dextrin with 300 g of anhydrous dextrose and 10 g of citric acid thoroughly in a Hobart mixer. The resulting blend was then manually fed into an 18 mm twin screw Leistritz extruder. The extruder barrel temperature was monitored in 6 zones according to the following table: Zone 1 50° C. Zone 2 160° C. Zone 3 180° C. Zone 4 200° C. Zone 5 200° C. Zone 6 (die head) 200° C.
  • Low shear extruder screws were used.
  • the extruder screw speed rate was 200 rpm.
  • a single, 3 mm die opening was used at the die head.
  • the motor load for the extruded sample was 50%.
  • An off-white solid material was extruded. The material was allowed to cool, and ground to a off-white powder.
  • the in vitro digestibility of the sample was 62% after 2.5 hours of enzyme treatment.
  • Example 29 was repeated, except that the extruder screw speed was 100 rpm.
  • the motor load was 75%.
  • a light yellow solid material was extruded, was allowed to cool, and was ground to a light yellow powder.
  • the in vitro digestibility of the sample was 67% after 2.5 hours of enzyme treatment.
  • Example 30 was repeated, except that the motor load was 50%. An off-white solid material was extruded, was allowed to cool, and was ground to an off-white powder. The in vitro digestibility of the sample was 43% after 2.5 hours of enzyme treatment.
  • Example 31 was repeated, except that the extruder screw speed was 200 rpm. The motor load remained at 50%. An off-white solid material was extruded, was allowed to cool, and was ground to an off-white powder. The in vitro digestibility of the sample was 43% after 2.5 hours of enzyme treatment Thus, it is seen that the invention provides a product that is improved in many respects over known products such as polydextrose. The product of the invention finds applicability as a bulking agent and in numerous other uses.
  • a mixture of MALTRIN® M180/hydrogenated MALTRIN® M180/dextrose monohydrate/citric acid (the dry solid weight ratio of maltodextrin:hydrogenated maltodexrin:dextrose being 2:2:1) is made by mixing 320 lbs of MALTRIN® M180, 320 lbs of hydrogenated MALTRIN® M180, 160 lbs of dextrose monohydrate and citric acid.
  • the hydrogenated maltodexrin is prepared according to WO 99/36442.
  • the resulting blend is then automatically fed into a 57 mm twin screw Wenger TX-57 extruder at a rate of 111 lbs per hour. Water is also fed to the extruder barrel at a rate of 12 lbs per hour.
  • the internal sample temperature at the die head is approximately 200 to 210° C.
  • Low shear extruder screws are used.
  • the extruder screw speed rate is 401 rpm.
  • a single, 17 mm dye opening is used at the die head.
  • the percent motor load for the extruded sample is 56%.
  • a vacuum of 13 inches of water (0.57 atm) is used.
  • the extruded solids are allowed to cool and ground to a powder.
  • Example 33 is repeated, except that corn starch is used in place of the hydrogenated MALTRIN® M180.
  • the hydrogenated maltodexrin is prepared according to WO 99/36442. The extruded solids are allowed to cool and ground to a powder.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Molecular Biology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mycology (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Saccharide Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
US10/874,686 2002-06-21 2004-06-22 Dextrinized, saccharide-derivatized oligosaccharides Abandoned US20050048191A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/874,686 US20050048191A1 (en) 2003-06-23 2004-06-22 Dextrinized, saccharide-derivatized oligosaccharides
US11/292,246 US20060149053A1 (en) 2002-06-21 2005-12-01 Dextrinized, saccharide-derivatized oligosaccharides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48204503P 2003-06-23 2003-06-23
US10/874,686 US20050048191A1 (en) 2003-06-23 2004-06-22 Dextrinized, saccharide-derivatized oligosaccharides

Related Child Applications (1)

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US11/292,246 Continuation-In-Part US20060149053A1 (en) 2002-06-21 2005-12-01 Dextrinized, saccharide-derivatized oligosaccharides

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US20050048191A1 true US20050048191A1 (en) 2005-03-03

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US10/874,686 Abandoned US20050048191A1 (en) 2002-06-21 2004-06-22 Dextrinized, saccharide-derivatized oligosaccharides

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Country Link
US (1) US20050048191A1 (de)
EP (1) EP1636271A1 (de)
CA (1) CA2530379A1 (de)
WO (1) WO2005000905A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013015890A1 (en) 2011-07-26 2013-01-31 Grain Processing Corporation Production of resistant dextrins
US10844139B2 (en) 2014-03-26 2020-11-24 Cargill, Incorporated Carbohydrate composition and process for making a carbohydrate composition

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060149053A1 (en) * 2002-06-21 2006-07-06 Grain Processing Corporation Dextrinized, saccharide-derivatized oligosaccharides
US8361235B2 (en) 2008-05-09 2013-01-29 Cargill, Incorporated Low-viscosity reduced-sugar syrup, methods of making, and applications thereof
US9730464B2 (en) 2008-05-09 2017-08-15 Cargill, Incorporated Carbohydrate compositions
DE102011056679A1 (de) * 2011-12-20 2013-06-20 Studiengesellschaft Kohle Mbh Verfahren zur säurekatalysierten Oligomerisation von Mono- oder Disacchariden
GB2499463B (en) 2012-01-31 2014-04-02 Verenium Corp Reduced sugar syrups and methods of making reduced sugar syrups
US10681928B2 (en) 2012-02-17 2020-06-16 Conagra Foods Rdm, Inc. Food product and coating
US11291222B2 (en) 2013-03-15 2022-04-05 Cargill, Incorporated Carbohydrate compositions
WO2021030434A1 (en) * 2019-08-12 2021-02-18 Matthew Sillick Whole grain syrups and flours
CN114621360B (zh) * 2022-03-25 2023-03-14 南京澜大生环境科技有限公司 一种连续制备抗性糊精膳食纤维方法

Citations (11)

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US3766165A (en) * 1966-08-17 1973-10-16 Pfizer Polysaccharides and their preparation
US3876794A (en) * 1972-12-20 1975-04-08 Pfizer Dietetic foods
US4820534A (en) * 1984-03-19 1989-04-11 General Foods Corporation Fixation of volatiles in extruded glass substrates
US4840807A (en) * 1987-08-24 1989-06-20 Sanmatsu Kogyo Kabushiki Kaisha Branched dextrin production and compositions containing same
US5009900A (en) * 1989-10-02 1991-04-23 Nabisco Brands, Inc. Glassy matrices containing volatile and/or labile components, and processes for preparation and use thereof
US5051500A (en) * 1989-08-11 1991-09-24 A. E. Staley Manufacturing Company Method of preparing a randomly-bonded polysaccharide
US5080919A (en) * 1985-02-15 1992-01-14 Nabisco Brands, Inc. Cookies with reduced sucrose content and doughs for production thereof
US5302462A (en) * 1992-03-09 1994-04-12 Morton International, Inc. Shelf-stable polyester/HMMM powder coating
US5389395A (en) * 1992-12-04 1995-02-14 Abbott Laboratories Nutritional bar for a protein-sparing diet of the very-low-calorie type
US5518739A (en) * 1994-07-20 1996-05-21 The Wm. Wrigley Jr. Company Chewing gum containing low levels of maltodextrin
US6630586B1 (en) * 1998-12-04 2003-10-07 Roquette Freres Branched maltodextrins and method of preparing them

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE56300B1 (en) * 1984-03-19 1991-06-05 Gen Foods Corp Method for fixing volatile flavorants in extruded vitreous substrates
JPS63214193A (ja) * 1987-03-03 1988-09-06 Sapporo Breweries Ltd ６−グルコシルマルトオリゴ糖誘導体の製法およびそれを用いるα−アミラ−ゼ活性測定法
CA2318604C (en) * 1998-01-20 2007-04-10 Grain Processing Corporation Reduced malto-oligosaccharides
CA2490092A1 (en) * 2002-06-21 2003-12-31 Grain Processing Corporation Dextrinized, saccharide-derivatized oligosaccharides

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3766165A (en) * 1966-08-17 1973-10-16 Pfizer Polysaccharides and their preparation
US3876794A (en) * 1972-12-20 1975-04-08 Pfizer Dietetic foods
US4820534A (en) * 1984-03-19 1989-04-11 General Foods Corporation Fixation of volatiles in extruded glass substrates
US5080919A (en) * 1985-02-15 1992-01-14 Nabisco Brands, Inc. Cookies with reduced sucrose content and doughs for production thereof
US4840807A (en) * 1987-08-24 1989-06-20 Sanmatsu Kogyo Kabushiki Kaisha Branched dextrin production and compositions containing same
US5051500A (en) * 1989-08-11 1991-09-24 A. E. Staley Manufacturing Company Method of preparing a randomly-bonded polysaccharide
US5009900A (en) * 1989-10-02 1991-04-23 Nabisco Brands, Inc. Glassy matrices containing volatile and/or labile components, and processes for preparation and use thereof
US5302462A (en) * 1992-03-09 1994-04-12 Morton International, Inc. Shelf-stable polyester/HMMM powder coating
US5389395A (en) * 1992-12-04 1995-02-14 Abbott Laboratories Nutritional bar for a protein-sparing diet of the very-low-calorie type
US5518739A (en) * 1994-07-20 1996-05-21 The Wm. Wrigley Jr. Company Chewing gum containing low levels of maltodextrin
US6630586B1 (en) * 1998-12-04 2003-10-07 Roquette Freres Branched maltodextrins and method of preparing them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013015890A1 (en) 2011-07-26 2013-01-31 Grain Processing Corporation Production of resistant dextrins
US10844139B2 (en) 2014-03-26 2020-11-24 Cargill, Incorporated Carbohydrate composition and process for making a carbohydrate composition

Also Published As

Publication number Publication date
WO2005000905A1 (en) 2005-01-06
CA2530379A1 (en) 2005-01-06
EP1636271A1 (de) 2006-03-22

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